US5667956A - Silver halide recording material - Google Patents

Silver halide recording material Download PDF

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Publication number
US5667956A
US5667956A US08/699,466 US69946696A US5667956A US 5667956 A US5667956 A US 5667956A US 69946696 A US69946696 A US 69946696A US 5667956 A US5667956 A US 5667956A
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US
United States
Prior art keywords
layer
silver halide
sensitive
recording material
halide emulsion
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
US08/699,466
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English (en)
Inventor
Michael Missfeldt
Johannes Willsau
Ralf Buscher
Peter Bell
Hans-Ulrich Borst
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AGFA
Agfa Gevaert AG
Original Assignee
AGFA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
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Assigned to AGFA-GEVAERT AG reassignment AGFA-GEVAERT AG ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BORST, HANS-ULRICH, BELL, PETER, BUSCHER, RALF, MISSFELDT, MICHAEL, WILLSAU, JOHHANNES
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/34—Fog-inhibitors; Stabilisers; Agents inhibiting latent image regression
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/062—Organo-phosphoranes without P-C bonds
    • C07F9/065—Phosphoranes containing the structure P=N-
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives

Definitions

  • This invention relates to a photographic recording material having at least one silver halide emulsion layer and optionally further layers, which material contains a compound of the general formula I in at least one of its layers.
  • the material exhibits improved grain at constant sensitivity and with a lower increase in fog on storage.
  • Core/shell emulsions having a certain iodide content in the core are described as grain reducing in WO 91/12 566 and EP-A-0 557 695.
  • An entirely different measure for reducing grain namely the use of DIP, compounds, is described in EP-A-0 446 863 and EP-A-0 507 092.
  • Certain coupler structures may also have a favourable effect, as is described in EP-A-0 422 595 and EP-A-0 566 115.
  • EP-A-0 377 181 describes the reaction of developer oxidation product (DOP) with certain compounds adhering to the grain as the reason for an improved sensitivity/grain ratio.
  • DOP developer oxidation product
  • grain may be improved by the addition of at least one compound of the general formula I, without degrading sensitivity or any other important photographic property; a reduced increase in fog on storage was also observed.
  • the present invention provides a photosensitive photographic recording material having at least one photosensitive silver halide layer and optionally further layers, characterised in that it contains a compound of the general formula I in at least one of its layers ##STR3## in which: Y 1 , Y 2 , Y 3 each mean one of the following residues ##STR4## R 1 to R 34 mean H, alkyl or aryl; two residues (R 1 to R 34 ) located on the same N atom may complete a 5-, 6- or greater-membered ring containing at least one N atom and optionally further heteroatoms; two residues (R 1 to R 34 ) located on adjacent N atoms may complete a ring involving both N atoms and at least one P atom;
  • X - means an anion required to balance the charge, for example Cl - , Br - or tosylate (TosO - ).
  • alkyl or aryl residues represented by R 1 to R 34 may optionally be substituted, for example with chlorine.
  • Alkyl residues preferably have up to 6 C atoms; examples are methyl, ethyl, isopropyl, butyl, tertiary butyl ( t Bu), hexyl.
  • Examples of completed heterocyclic rings are pyrrolidine, piperidine, morpholine, piperazine, 1,3-diaza-2-phosphacyclopentane, 1,3-diaza-2-phosphacyclohexane and 1,3-diaza-2-phosphacycloheptane rings.
  • Suitable examples of the compounds used according to the invention are shown below: ##STR5##
  • the phosphazene salts containing only one P atom were produced as described in BE 671 026. Phosphazenes with 2 and more P atoms could be synthesised by analogy with the synthetic methods described by R. Schwesinger in Angew. Chem., 103, 1376 (1991) and Angew. Chem., 105, 1420 (1993).
  • the compounds to be used according to the invention are added to the casting solutions for the layers concerned as an aqueous solution, wherein the compounds may be used individually or as a blend of two or more thereof. They may be added to one or more of the photosensitive layers, namely to a blue-sensitive, a green-sensitive and/or a red-sensitive silver halide emulsion layer or alternatively also to a non-photosensitive binder layer adjacent to one of the above-stated layers. They may advantageously be added both to one of the stated photosensitive silver halide emulsion layers and to a non-photosensitive binder layer adjacent thereto.
  • the quantity of the added substance is preferably between 1 and 200 mg/m 2 .
  • the recording material according to the invention has an improved grain/sensitivity ratio, i.e. grain is improved without impairing sensitivity. A lower increase in fog on storage is also observed.
  • colour photographic materials are colour negative films, colour reversal films, colour positive films, colour photographic paper, colour reversal photographic paper, colour-sensitive materials for the dye diffusion transfer process or the silver dye bleaching process.
  • the photographic materials consist of a support onto which at least one photosensitive silver halide emulsion layer is applied. Thin films and sheets are in particular suitable as supports. A review of support materials and the auxiliary layers applied to the front and reverse sides of which is given in Research Disclosure 37254, part 1 (1995), page 285.
  • the colour photographic materials conventionally contain at least one red-sensitive, one green-sensitive and one blue-sensitive silver halide emulsion layer, optionally together with interlayers and protective layers.
  • these layers may be differently arranged. This is demonstrated for the most important products:
  • Colour photographic films such as colour negative films and colour reversal films have on the support, in the stated sequence, 2 or 3 red-sensitive, cyan-coupling silver halide emulsion layers, 2 or 3 green-sensitive, magenta-coupling silver halide emulsion layers and 2 or 3 blue-sensitive, yellow-coupling silver halide emulsion layers.
  • the layers of identical spectral sensitivity differ with regard to their photographic sensitivity, wherein the less sensitive partial layers are generally arranged closer to the support than the more highly sensitive partial layers.
  • a yellow filter layer is conventionally located between the green-sensitive and blue-sensitive layers to prevent blue light from reaching the underlying layers.
  • Colour photographic paper which is usually substantially less photosensitive than a colour photographic film, conventionally has on the support, in the stated sequence, one blue-sensitive, yellow-coupling silver halide emulsion layer, one green-sensitive, magenta-coupling silver halide emulsion layer and one red-sensitive, cyan-coupling silver halide emulsion layer; the yellow filter layer may be omitted.
  • the number and arrangement of the photosensitive layers may be varied in order to achieve specific results. For example, all high sensitivity layers may be grouped together in one package of layers and all low sensitivity layers may be grouped together another package of layers in order to increase sensitivity (DE 25 30 645).
  • the substantial constituents of the photographic emulsion layers are binder, silver halide grains and colour couplers.
  • Photographic materials with camera sensitivity conventionally contain silver bromide-iodide emulsions, which may optionally also contain small proportions of silver chloride.
  • Photographic print materials contain either silver chloride-bromide emulsions with up to 80 mol. % of AgBr or silver chloride-bromide emulsions with above 95 mol. % of AgCl.
  • the maximum absorption of the dyes formed from the couplers and the developer oxidation product is preferably within the following ranges: yellow coupler 430 to 460 nm, magenta coupler 540 to 560 nm, cyan coupler 630 to 700 nm.
  • Colour couplers which are usually hydrophobic, as well as other hydrophobic constituents of the layers, are conventionally dissolved or dispersed in high-boiling organic solvents. These solutions or dispersions are then emulsified into an aqueous binder solution (conventionally a gelatine solution) and, once the layers have dried, are present as fine droplets (0.05 to 0.8 ⁇ m in diameter) in the layers.
  • aqueous binder solution conventionally a gelatine solution
  • fine droplets 0.05 to 0.8 ⁇ m in diameter
  • the non-photosensitive interlayers generally located between layers of different spectral sensitivity may contain agents which prevent an undesirable diffusion of developer oxidation products from one photosensitive layer into another photosensitive layer with a different spectral sensitisation.
  • Suitable compounds may be found in Research Disclosure 37254, part 7 (1995), page 292 and in Research Disclosure 37038, part III (1995), page 84.
  • the photographic material may also contain UV light absorbing compounds, optical whiteners, spacers, filter dyes, formalin scavengers, light stabilisers, antioxidants, D min dyes, additives to improve stabilisation of dyes, couplers and whites and to reduce colour fogging, plasticisers (latices), biocides and others.
  • Suitable compounds may be found in Research Disclosure 37254, part 8 (1995), page 292 and in Research Disclosure 37038, parts IV, V, VI, VII, X, XI and XIII (1995), pages 84 et seq.
  • the layers of colour photographic materials are conventionally hardened, i.e. the binder used, preferably gelatine, is crosslinked by appropriate chemical methods.
  • Suitable hardener substances may be found in Research Disclosure 37254, part 9 (1995), page 294 and in Research Disclosure 37038, part XII (1995), page 86.
  • a colour photographic recording material for colour negative development was produced (layer structure 1A) by applying the following layers in the stated sequence onto a transparent cellulose triacetate layer support. All stated quantities relate to 1 m 2 .
  • the applied quantity of silver halide is stated as the corresponding quantities of AgNO 3 .
  • All the silver halide emulsions were stabilised with 0.1 g of 4-hydroxy-6-methyl-1,3,3a,7-tetraazaindene per 100 g of AgNO 3 .
  • TCP tricresyl phosphate
  • micerate silver bromide-iodide emulsion (0.5 mol. % iodide; average grain diameter 0.07 ⁇ m) prepared from 0.25 g of AgNO 3 with
  • Red-sensitised silver bromide-iodide emulsion (4 mol. % iodide; average grain diameter 0.5 ⁇ m) prepared from 2.7 g of AgNO 3 with
  • Red-sensitised silver bromide-iodide emulsion (12 mol. % iodide; average grain diameter 1.0 ⁇ m) prepared from 2.2 g of AgNO 3 with
  • Green-sensitised silver bromide-iodide emulsion (4 mol. % iodide; average grain diameter 0.35 ⁇ m) prepared from 1.9 g of AgNO 3 with
  • Green-sensitised silver bromide-iodide emulsion (9 mol. % iodide; average grain diameter 0.8 ⁇ m) prepared from 1.25 g of AgNO 3 with
  • micerate silver bromide-iodide emulsion (0.5 mol. % iodide; average grain diameter 0.06 ⁇ m) prepared from 0.06 g of AgNO 3 , with
  • Layers structures 1B to 1D differ by the addition of a substance according to the invention to the 7th layer.
  • Table 1 summarises the substances used, quantities and results:
  • the materials according to the invention exhibit an improvement in grain without degradation of sensitivity.
  • a lower increase in fog on storage is also observed in the materials according to the invention.
  • Layer structure 2A differs from layer structure 1A of Example 1 in the composition of the 8th layer.
  • Layer structures 2B to 2D differ by the addition of V-16 to layers 4 or 5.
  • Table 2 summarises the location and quantity of the addition and the results:
  • the materials according to the invention exhibit an improvement in grain without degradation of sensitivity.
  • a lower increase in fog on storage is also observed in the materials according to the invention.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US08/699,466 1995-08-29 1996-08-19 Silver halide recording material Expired - Fee Related US5667956A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19531688.6 1995-08-29
DE19531688A DE19531688A1 (de) 1995-08-29 1995-08-29 Silberhalogenidaufzeichnungsmaterial

Publications (1)

Publication Number Publication Date
US5667956A true US5667956A (en) 1997-09-16

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Family Applications (1)

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US08/699,466 Expired - Fee Related US5667956A (en) 1995-08-29 1996-08-19 Silver halide recording material

Country Status (4)

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US (1) US5667956A (fr)
EP (1) EP0762202B1 (fr)
JP (1) JPH09120125A (fr)
DE (2) DE19531688A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20030036667A1 (en) * 2001-06-15 2003-02-20 Marielouise Henrich Process for preparing nuclear-fluorinated aromatics
US6562557B2 (en) * 2000-07-21 2003-05-13 Agfa-Gevaert Color photographic silver halide material
EP3763721A4 (fr) * 2018-03-07 2021-11-10 Tosoh Corporation Sel de phosphazénium divalent, composition d'oxyde de polyalkylène contenant celui-ci, et composition de formation de polyuréthane contenant ladite composition d'oxyde de polyalkylène

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7135366B2 (ja) * 2018-03-26 2022-09-13 東ソー株式会社 ２価のホスファゼニウム塩およびその製造方法
WO2019172266A1 (fr) * 2018-03-07 2019-09-12 東ソー株式会社 Sel de phosphazénium divalent, composition d'oxyde de polyalkylène contenant celui-ci, et composition de formation de polyuréthane contenant ladite composition d'oxyde de polyalkylène
JP7135367B2 (ja) * 2018-03-26 2022-09-13 東ソー株式会社 ポリアルキレンオキシド組成物および該ポリアルキレンオキシド組成物を含むポリウレタン形成性組成物

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271175A (en) * 1963-12-04 1966-09-06 Eastman Kodak Co Aziridinyl phosphonitrile gelatin hardening agent
FR1486986A (fr) * 1965-07-28 1967-06-30 Eastman Kodak Co Nouvelles compositions de gélatine et leurs applications, notamment en photographie
US4668616A (en) * 1984-11-28 1987-05-26 Fuji Photo Film Co., Ltd. Process for hardening gelatin
EP0304296A2 (fr) * 1987-08-20 1989-02-22 EASTMAN KODAK COMPANY (a New Jersey corporation) Elément photographique à base de composés polyphosphazène antistatiques
WO1990008978A1 (fr) * 1989-02-03 1990-08-09 Eastman Kodak Company Composition antistatique a base de phosphazene cyclique et de sel
US4988615A (en) * 1988-02-10 1991-01-29 Minnesota Mining And Manufacturing Company Stabilizers for photographic emulsions
US5573900A (en) * 1994-05-20 1996-11-12 Fuji Photo Film Co., Ltd. Dispersion method of hydrophobic, photographically useful compound

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3271175A (en) * 1963-12-04 1966-09-06 Eastman Kodak Co Aziridinyl phosphonitrile gelatin hardening agent
FR1486986A (fr) * 1965-07-28 1967-06-30 Eastman Kodak Co Nouvelles compositions de gélatine et leurs applications, notamment en photographie
US4668616A (en) * 1984-11-28 1987-05-26 Fuji Photo Film Co., Ltd. Process for hardening gelatin
EP0304296A2 (fr) * 1987-08-20 1989-02-22 EASTMAN KODAK COMPANY (a New Jersey corporation) Elément photographique à base de composés polyphosphazène antistatiques
US4988615A (en) * 1988-02-10 1991-01-29 Minnesota Mining And Manufacturing Company Stabilizers for photographic emulsions
WO1990008978A1 (fr) * 1989-02-03 1990-08-09 Eastman Kodak Company Composition antistatique a base de phosphazene cyclique et de sel
US5573900A (en) * 1994-05-20 1996-11-12 Fuji Photo Film Co., Ltd. Dispersion method of hydrophobic, photographically useful compound

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6562557B2 (en) * 2000-07-21 2003-05-13 Agfa-Gevaert Color photographic silver halide material
US20030036667A1 (en) * 2001-06-15 2003-02-20 Marielouise Henrich Process for preparing nuclear-fluorinated aromatics
US7091362B2 (en) 2001-06-15 2006-08-15 Bayer Aktiengesellschaft Process for preparing nuclear-fluorinated aromatics
US7247733B2 (en) 2001-06-15 2007-07-24 Lanxess Deutschland Gmbh Process for preparing nuclear-fluorinated aromatics
EP3763721A4 (fr) * 2018-03-07 2021-11-10 Tosoh Corporation Sel de phosphazénium divalent, composition d'oxyde de polyalkylène contenant celui-ci, et composition de formation de polyuréthane contenant ladite composition d'oxyde de polyalkylène

Also Published As

Publication number Publication date
DE19531688A1 (de) 1997-03-06
EP0762202A1 (fr) 1997-03-12
JPH09120125A (ja) 1997-05-06
DE59603966D1 (de) 2000-01-27
EP0762202B1 (fr) 1999-12-22

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Owner name: AGFA-GEVAERT AG, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:MISSFELDT, MICHAEL;WILLSAU, JOHHANNES;BUSCHER, RALF;AND OTHERS;REEL/FRAME:008173/0420;SIGNING DATES FROM 19960614 TO 19960618

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FP Lapsed due to failure to pay maintenance fee

Effective date: 20010916

STCH Information on status: patent discontinuation

Free format text: PATENT EXPIRED DUE TO NONPAYMENT OF MAINTENANCE FEES UNDER 37 CFR 1.362